反应详情

To a solution of 6,6-dimethyl 3-ethyl-4,5,6,7-tetrahydro-1H-indol-4-one (50 mg, 0.26 mmol) in DMF (4 mL) at 0° C., was added NaH (11 mg of a 60% dispersion in mineral oil, 0.29 mmol). The cooling bath was removed and the mixture stirred at room temperature for 20 min. After this time 2-fluoropyridine (26 μl, 0.29 mmol) was added and the residue heated at 90° C. for 6 h. The solvent was evaporated and the residue partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed an silica gel, eluting with hexane:EtOAc (2:1), to give the title pyrrole (18 mg, 26%) as a colourless solid. mp 125-127° C. 1H NMR (360 MHz, CDCl3) δ 1.10 (6H,s), 1.23 (3H,t,J=7.4 Hz), 2.38 (2H,s), 2.83 (2H,d of q, J=7.4 and 1.0 Hz), 2.92 (2H,s), 6.88 (1H,s), 7.25-7.27 (1H,m), 7.30 (1H,d,J=8.0 Hz), 7.82 (1H,d of t, J=7.7 and 1.9 Hz), 8.51-8.57 (1H,m). MS (ES+) 269 (M+1).

1. customThe cooling bath was removed
2. temperaturethe residue heated at 90° C. for 6 h
3. customThe solvent was evaporated
4. customthe residue partitioned between EtOAc (20 mL) and water (20 mL)
5. customThe organic layer was separated
6. dry with materialdried (Na2SO4)
7. customevaporated
8. customThe residue was chromatographed an silica gel
9. washeluting with hexane:EtOAc (2:1)